103495-72-3Relevant academic research and scientific papers
Reactions of Uracils, 7. Synthesis and Novel Consecutive Thermal -Sigmatropic Rearrangements of 6-(Alkylamino)-5-ethenyluracils
Matyus, Peter,Zolyomi, Gabor,Eckhardt, Gert,Wamhoff, Heinrich
, p. 943 - 949 (2007/10/02)
Additional 6-(alkylamino)-5-ethenyluracils (2d, 7) have been prepared for investigating substituent effects in thermal reactions.Like 2a, upon heating in Dowtherm A 2d and 7 afford after saponification 6-amino-5-(ethoxycarbonylethyl)uracils 4 and 8, respectively.After refluxing in xylene the intermediary imines 11 and 12 can be isolated.Deuteration experiments reveal consecutive thermal H-migrations (2a-D1 -> 4-D1 and 4-D2; 2a'-D2 -> 4'-D1).The mechanism is discussed.
